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Microbial metabolism part 9. Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones.
Chem Pharm Bull (Tokyo). 2008 Apr; 56(4):418-22.CP

Abstract

5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4'-hydroxychrysin (4), chrysin 7-O-beta-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4'-hydroxy-3'-methoxychrysin (chrysoeriol) (7), 4'-hydroxychrysin (apigenin) (4) 3',4'-dihydroxychrysin (luteolin) (8), 3'-methoxychrysin 4'-O-alpha-D-6-deoxyallopyranoside (9), chrysin 4'-O-alpha-D-6-deoxyallopyranoside (10), and luteolin 3'-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4'-dihydroxyflavone (12) and 4'-hydroxyflavone 5-O-beta-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-beta-D-4-O-methylglucopyranoside (15) and (+/-)-flavanone 6-O-beta-D-4-O-methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed.

Authors+Show Affiliations

National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

18379084

Citation

Herath, Wimal, et al. "Microbial Metabolism Part 9. Structure and Antioxidant Significance of the Metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones." Chemical & Pharmaceutical Bulletin, vol. 56, no. 4, 2008, pp. 418-22.
Herath W, Mikell JR, Hale AL, et al. Microbial metabolism part 9. Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones. Chem Pharm Bull. 2008;56(4):418-22.
Herath, W., Mikell, J. R., Hale, A. L., Ferreira, D., & Khan, I. A. (2008). Microbial metabolism part 9. Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones. Chemical & Pharmaceutical Bulletin, 56(4), 418-22.
Herath W, et al. Microbial Metabolism Part 9. Structure and Antioxidant Significance of the Metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones. Chem Pharm Bull. 2008;56(4):418-22. PubMed PMID: 18379084.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Microbial metabolism part 9. Structure and antioxidant significance of the metabolites of 5,7-dihydroxyflavone (chrysin), and 5- and 6-hydroxyflavones. AU - Herath,Wimal, AU - Mikell,Julie Rakel, AU - Hale,Amber Lynn, AU - Ferreira,Daneel, AU - Khan,Ikhlas Ahmad, PY - 2008/4/2/pubmed PY - 2008/6/10/medline PY - 2008/4/2/entrez SP - 418 EP - 22 JF - Chemical & pharmaceutical bulletin JO - Chem. Pharm. Bull. VL - 56 IS - 4 N2 - 5,7-Dihydroxyflavone (chrysin) (1) when fermented with fungal cultures, Aspergillus alliaceous (ATCC 10060), Beauveria bassiana (ATCC 13144) and Absidia glauco (ATCC 22752) gave mainly 4'-hydroxychrysin (4), chrysin 7-O-beta-D-4-O-methylglucopyranoside (5) and chrysin 7-sulfate (6), respectively. Mucore ramannianus (ATCC 9628), however, transformed chrysin into six metabolites: 4'-hydroxy-3'-methoxychrysin (chrysoeriol) (7), 4'-hydroxychrysin (apigenin) (4) 3',4'-dihydroxychrysin (luteolin) (8), 3'-methoxychrysin 4'-O-alpha-D-6-deoxyallopyranoside (9), chrysin 4'-O-alpha-D-6-deoxyallopyranoside (10), and luteolin 3'-sulfate (11). Cultures of A. alliaceous (ATCC 10060) and B. bassiana (ATCC 13144) metabolized 5-hydroxyflavone (2) into 5,4'-dihydroxyflavone (12) and 4'-hydroxyflavone 5-O-beta-D-4-O-methylglucopyranoside (13), respectively. 6-Hydroxyflavone (3) was transformed into 6-hydroxyflavanone (14), flavone 3-O-beta-D-4-O-methylglucopyranoside (15) and (+/-)-flavanone 6-O-beta-D-4-O-methylglucopyranoside (16) by cultures of Beauveria bassiana (ATCC 13144). The structures of the metabolic products were elucidated by means of spectroscopic data. The significance of the metabolites as antioxidants in relation to their structure is briefly discussed. SN - 0009-2363 UR - https://www.unboundmedicine.com/medline/citation/18379084/Microbial_metabolism_part_9__Structure_and_antioxidant_significance_of_the_metabolites_of_57_dihydroxyflavone__chrysin__and_5__and_6_hydroxyflavones_ L2 - http://joi.jlc.jst.go.jp/JST.JSTAGE/cpb/56.418?from=PubMed DB - PRIME DP - Unbound Medicine ER -